Production of c-alkylated phenols



WALTER SCHOELLER, or BERLIN-cHAnLorrEnnun, iiaisis'jonimngorfnngifigijggi LITZ, AND REINHARD' CLERC, or BEnLm,"eiiRMAnY;"nssrano ts'IQLTHEQQEBQM? SCHERING-KAHLZBAUM A. a, oF'BEnLIN.gEnmnN p PRODUCTION onc-nmz'gnn rnn r'annnonsf i f g No Drawing. Application filed April 4,1929, Serial No.352,300,end nflq 127 1. v

Our invention refers to the production of alkylated phenols and moreespecially to a method of producing C-alkylated phenols by hydrogenationof diphenyl methane deriva- 5 tives.

In a .copending application for patent of the United States Serial No.122,031, filed by Hans Jordan, is described a method of producingalkylated phenols by subjecting a dihydroxydiph'enyl methane derivativeat a temperature not materially exceeding 160 C. to treatment withhydrogen in the presence of a slow acting hydrogenation catalyst Wherebythe molecule of the condensation product is split up at the point wherethe ketone connects the two radicals.

In another application for patent of the United States Serial No.203,681, filed also by Hans Jordan, is disclosed a method of producingphenol compounds by treating a derivative of dihydroxydiphenyl methanewith hydrogen in the presence of a hydrogenation catalyst at atemperature of about 200 Cato eifect hydrogenation.

We have now ascertained that this mode of splitting up the. molecule byhydrogenation can be materially improved and hydrogenw,

tion inthe nucleus can be avoided, if the hydrogen is diluted eitherwith steam or with an inert gas, for instance nitrogen. We are thusenabled to attain greater reaction velocities by operating athigherftemperatures without the nucleus being hydrogenated.

' ,The catalyst used may for instance be a catalyst precipitated in theform of a carbonate or hydroxide, which has notbeen previously subjectedto reduction. Catalysts of this kind are converted into theircatalytically active form by acting thereon withhydrogen under pressurein a closed reaction vessel '(autoelave) whereby water is formed.

If this reduction of the catalyst is efi'ected simultaneously with thehydrogenation, the gas space of the autoclave, if the reaction iscarried out at a temperature of 190-200 C. and a working pressure ofabout 25 atmospheres will be filled with a mixture' containing aboutequal parts of hydrogen and water vapor (steam). 'Hydrogenation thustakes is the calculatedgone.

place inaquantitiveniannenand 'withoutthe I l nucleus;beingn.;any.yayafiected-a. i y

1' Dis-(.45 j ydroxyphenyt) dimethyljmethane is: reatedt n the 7. Pre eof "a out by: weight "of al carbonate or; hydroxide metat which;catalyses; hydrogenation, h

hydrogen under pressure-ate; temperaturegofr ebQutQQQ?-When-:the.quantity 'hy equired for hydrogenation and 911k? t g: 11.Qfithe; m l cnsumed the reactioncomes'gt @a standstill. By fractionation reaction pIOdfict p-i-sopropyl phenol and phenol are obtainedin the calculated quantities;

Ewample 2 Example 3 I Di- (-methyl-6hydroxyphenyl) dimethylniethaneistreated in the presence of about 3% by weight of a previouslyreduced hydrogenation catalyst in an autoclave at a temperature of about200 C. with hydrogen under pressure,ithe autoclave having been one thirdto one half of the working pressure. The reaction takes the coursedescribed with 1 previously filled withnitriogen up to about referenceto Examples 1 and 2-and theyield In asimilar manner other diphenylmethane derivatives, for, instance the dihydroxydiphenyl'alkyl methanesobtainable by condensation of aldehydes and phenols,flcan be treated.

Va'rious changes may be made inzthe de tails disclosed in the foregoingspecification I without departing from the invention or sacrificlng' theadvantages thereoi In the claims aflixed to this specification no 7' theinvention is intended to the exclusion of other modifications thereofand the right to selection of any particular modification ofsubsequentclly make claim to any modification not covere by these claimsis expressly reserved.

We claim g 1. The method of producing C-alkylated phenols comprisingacting at about 200 C.

under increased pressure on dih droxydiphenyl methane in the presence ahydrogenation catalyst with a mixture of hydro- 7 1o genandaninertgas. Va 2. The method of producing C-alkylated phenols comprising acting atabout 200 C. under increased pressure on dihydroxydiphenylymethane inthe presenceof a hydrogenation catalyst with a mixture of hydrogen andwater vapor.

3. The method of producing C-alkylated phenols comprising acting atabout 200 C. under increased pressure on dihydroxydiphenyl methane inthe prese'nce'of a metallic oxide the metal of which is a hydrogenationcatalyst, with hydrogen, the water vapor resultingfrom the reduction ofthe oxide being left in the reaction mixture. 2 In testimony whereof'we,aflix our'signatures. 7

r WALTER SCHOELLER HANS JORDAN. 1

; REINHARD CLERC.

